Reservations for our trip to Italy

If you are locked into your schedule and the hotel does not have a cancellation penalty do it now. We generally don't reserve much in advance because we like to stay flexible but others get fixated on having that reservation in hand. As for air, it is a dice roll. Who knows. If you like the price and schedule do it. The probability of being able to purchase the cheapest possible ticket is very low. Like buying stock. Will all of the current unrest in the middle east and the price of oil going up, some are suggesting that fares may not be coming down. But who really knows?

I would get both sooner rather than later. As in now. If you can be flexible on departure and return dates, you'll get a better fare. Good luck.

I agree with Frank on the hotel, although in some places you can call a few days in advance and find accommodations at smaller ones. Try to get a list from Rick's travel guides or this group. I took Rick's advice on that and it worked out fine. We were there in mid-September through the end of the month. It all depends on where you are. If you're going to a larger city such as Rome, Venice, Florence or Milan, try packaging your air and initial hotel through an airline. Sometimes you can save money on booth, but check out the hotels that are available through Trip Advisor or ask the folks on this site. If you're taking a train anywhere in Italy be sure you make reservations a few days out, and if it's the night train, at least two weeks in advance for a smaller sleeping berth. I waited to the last week and our threesome ended up sharing a six person berth with three others from Milan to Paris (one Parisian going home and two other Americans from SF). A truly unique experience and it went fine, but not really what I was looking for. Good luck on your trip. September/October is a great time of year to go.

Don, I personally like to get things done as soon as I have dates, just so it can be done with the big items and I can use the remaining time to fine tune smaller details. Also since flight and hotels are major components of your budget, it helps getting those settled so you know what you can spend (or can't spend!) on other things. We are also going in September and we already have our flight and apartment. As has been mentioned, flights are hard to determine so that depends on how much of a risk taker you are. As far as hotels go, I've been told by a few that now is too early to book for the fall and to contact them come summer, but others are willing to reserve, so test the waters and see if the place you like is accepting reservations this soon.